Chester Holidays from £867
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Chester Holiday
The best way to experience this vibrant city is with a custom-made Chester holiday package. Stay in the neighbourhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect holiday to Chester now.
Top Chester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Head of Pond House
£1,167
per person
14 Dec - 20 Dec
found 4 hours ago
Return flight included
London (LHR) to New Haven (HVN)
10/10 Exceptional! (13 reviews)
The cottage is quaint and old, it is showing its age. The beds were ever comfortable. The entertainment option was not a TV but a projector with a shoddy speaker. The spiral staircase to the upper level was treacherous to come down and several of the vertical supports were look making the decent and ascent scary. The pond side location was very nice and the little patio was special apart from the chainsaws from the unfortunately scheduled tree cutting by neighbors.
Reviewed on 23 Sept 2026
Hyatus Luxury Residences City Crossing
The Hill
£1,045
per person
5 Dec - 12 Dec
found 20 hours ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on 10 Aug 2026
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 1,550 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park |
Top hotels in Chester
Regency Inn & Suites New London, Mystic
269 North Frontage Road New London CT
Fully refundableReserve now, pay when you stay
£84
29 Sept - 30 Sept
includes taxes & fees
6/10 (1,007 reviews)
"This was kind of an interesting property with lots of attached and detached buildings making up the total. All of the outer doors looked like they had new electric locks installed but the new mechanisms left huge unfilled holes in the door frames. While the pool was open, the lights were off, and ..."
Reviewed on 27 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
£68
29 Sept - 30 Sept
includes taxes & fees
8/10 Very good! (1,014 reviews)
"It was a decent stay, we came in for a family reunion and originally planning to camp but weren’t able to due to the storm so we found this last min at a decent price point. Staff was very friendly when we came in, seems to be family operated which I like. Room was clean could use some updates but ..."
Reviewed on 27 Sept 2026
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
£96
5 Oct - 6 Oct
includes taxes & fees
9/10 Wonderful! (2,773 reviews)
"Charged me twice ??"
Reviewed on 28 Sept 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chester attractions
Norma Terris Theater
The Norma Terris Theatre is Goodspeed Musicals' developmental space where innovative productions debut. In this intimate setting, audiences witness tomorrow's Broadway hits evolve before their eyes.
Frequently asked questions
How much does a Chester travel package cost?
Maybe less than you imagined — from a low £867, actually! By bundling flights, hotels and car rentals into a custom-built package, your trip to Chester is only clicks away.
If I'm not able to travel, can I cancel my Chester travel package?
You can. We totally understand that even the best-laid plans can fail, so we're here to help if you have to make changes to your Chester travel package. It may be possible to cancel or amend your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Chester?
Combine your bookings with Expedia to save big on your next trip. With over 550 air carriers and 1,000,000 properties across the globe, your Chester travel package can be tailored exactly to suit your budget. With all that extra money, why not include one or more interesting tours and activities? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Chester is much closer than you thought!
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:
- Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
- Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your booking and then start working on your travel itinerary.
Where should I stay in Chester?
With loads to explore in Chester, we suggest you stay near its attractions. Norma Terris Theatre, Chester Creek Marina and Plattwood Park are some good ones to add to your itinerary.
What are the top hotels in Chester?
Saybrook Point Resort & Marina and Pier Blue Inn Old Saybrook - Essex are among the most popular hotels in Chester. Why not check out the amenities and facilities at each and then make a decision?
How far in advance should I book my Chester holiday?
Search Expedia to compare international flights as soon as you know your travel dates. You can generally purchase a ticket up to a year prior to departure. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Chester sometimes appear a few weeks before the date of departure.
What does an Expedia Chester travel package include?
From hotels and flights to rental cars, Expedia can help you put together a Chester package that's ideal for you. Heading away for a few weeks? Check out a rental car, flight and hotel bundle. If you're taking a short break, a flight and hotel deal may suit you better. Experiences can also be added once you've made your booking. Our packages make it a breeze to save and plan.
What should I know before booking a Chester travel package?
Tailor deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we've got everything you need to plan your getaway. You'll save a packet just for bundling your bookings. Whether you're going on a snow and ski adventure or drinking cocktails on a beach, your ideal getaway is only clicks away.
Can I choose my airline with a Chester Expedia travel package?
Yes, so take your pick! We have access to over 550 airlines around the world, so you can design your Chester getaway according to your style and budget.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
